EP1934272B1 - Élastomère polyuréthane - Google Patents

Élastomère polyuréthane Download PDF

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Publication number
EP1934272B1
EP1934272B1 EP06799745A EP06799745A EP1934272B1 EP 1934272 B1 EP1934272 B1 EP 1934272B1 EP 06799745 A EP06799745 A EP 06799745A EP 06799745 A EP06799745 A EP 06799745A EP 1934272 B1 EP1934272 B1 EP 1934272B1
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EP
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Prior art keywords
propanediol
tri
polyurethane elastomer
diisocyanate
elastomer according
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EP06799745A
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German (de)
English (en)
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EP1934272A4 (fr
EP1934272A1 (fr
Inventor
Jesper FAHLÉN
Birger Midelf
Anders Magnusson
Kent SÖRENSEN
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Perstorp Specialty Chemicals AB
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Perstorp Specialty Chemicals AB
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/44—Polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/302—Water
    • C08G18/307—Atmospheric humidity
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic

Definitions

  • the present invention relates to a polyurethane elastomer obtained by reacting at the least a minimum of three basic compounds, said compounds being a di, tri or polyisocyanate, a polycarbonate diol of a 2-alkyl-1,3-propanediol, a 2,2-dialkyl-1,3-propanediol, an alkoxylated 2-alkyl-1,3-propanediol and/or an alkoxylated 2,2-dialkyl-1,3-propanediol, and a di, tri or polyalcohol.
  • polyurethane elastomers are primarily determined by the chemical composition although the properties also depend on the processing methods used for production. Variation of the basic starting materials yields elastomeric products which to a large extent are characterised by a segmented, hard and soft, block structure formed by the primary chain.
  • the hard segments are formed by the reaction of a di, tri or polyisocyanate with a di, tri or polyhydric compound.
  • the di, tri or polyhydric compounds used in polyurethane elastomers today are mainly polyester and polyether based.
  • the advantages with polyester based over polyethers based are structural strength, oil, solvent and oxygen resistance and the advantages with polyether based are hydrolytic resistance and low temperature flexibility.
  • the melting temperature of the hard segment and the amount of this segment determines the dimensional thermal stability of a polyurethane elastomer. Interchain interactions (hydrogen bonds mostly) of the hard segments contribute to the high tensile strength, elongation, tear strength and set values obtained.
  • the soft segments result from a long chain di, tri or polyalcohol and the mobility of these segments are responsible for the reversible elastomeric properties.
  • the low temperature flexibility, solvent and UV resistance are largely controlled by the long flexible soft segments in the polyurethane elastomer.
  • Various types of di, tri and polyalcohols have been used and/or evaluated in order to tailor the properties of elastomers.
  • di, tri and polyalcohols have molecular weights usually in the range of 600-2500.
  • Di, tri or polyalcohols typically used for polyurethane elastomers have a linear structure and two reactive hydroxyl groups.
  • the morphology (secondary and tertiary structures) of a polyurethane elastomer is dependent on the length and chemical structure of said segments.
  • the exceptional properties of polyurethane elastomers are due to the two or polyphase structure.
  • polyhydric compounds such as polycarbonate and polycaprolactone diols, triols and polyols with, compared to polyester diols, triols and polyols, improved UV, chemical, hydrolytic, oxygen and thermal resistance, but with retained mechanical properties.
  • Polycarbonate diols typically polyester polycarbonate diols, have been shown to have excellent UV, chemical, hydrolytic and oxygen resistance with mechanical properties comparable to those obtained with polyester diols.
  • Polyester polycarbonate diols are in polyurethane elastomers used to a larger extent in areas wherein produced articles are used in applications wherein hydrolytic stability and resistance to micro-organisms are crucial, such as in outdoor tubes and pipes, sport and leisure applications, rollers for printers and paper machines.
  • Polycarbonate diols and polyurethanes prepared using polycarbonate diols are disclosed in for instance
  • the present invention quite unexpectedly provides a polyurethane elastomer with improved properties over prior art elastomers.
  • the polyurethane elastomer of the present invention is obtained by reacting at the least a di, tri or polyisocyanate, a polycarbonate diol of a 2,2-dialkyl-1,3-propanediol, an alkoxylated 2,2-dialkyl-1,3-propanediol and/or a polycarbonate diol comprising units from said 1,3-propanediol and a di, tri or polyalcohol.
  • Di, tri and polyalcohol are herein to be understood as linear or branched, aliphatic, cycloaliphatic or aromatic di, tri and polyhydric alcohols and dimers, trimers and polymers comprising units from one or more di, tri or polyhydric alcohols and/or one or more alkylene oxides.
  • Alkyl in said 1,3-propanediols is preferably linear or branched saturated aliphatic alkanyl having 1-8 carbon atoms and alkoxylated is likewise preferably ethoxylated, propoxylated and/or butoxylated having 1-20 alkoxy units.
  • Said polycarbonate diol is at least one polycarbonate diol of 2-ethyl-2-butyl-1,3-propanediol, or is at least one polycarbonate diol comprising units from said 1,3-propanediol.
  • Said polycarbonate diol has a molecular weight of 500-5000, such as 500-2500 and can suitably be obtained from for example said 1,3-propanediol and a carbon dioxide source, such as dimethyl carbonate, diethyl carbonate and/or urea.
  • the di, tri or polyisocyanate is in preferred embodiments an aliphatic, cycloaliphatic and/or aromatic di, tri or polyisocyanate, such as hexamethylene diisocyanate 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, tetramethylxylylene diisocyanate, 1,6-hexane diisocyanate, trimethylhexane diisocyanate, 1,12-dodecane diisocyanate, cyclohexane diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate and/or nonane triisocyanate.
  • Said di, tri or polyalcohol as defined above is preferably at least one 1, ⁇ -diol, 2-alkyl-1,3-propanediol, 2,2-dialkyl-1,3-propanediol, 2-alkyl-2-hydroxyalkyl-1,3-propanediol and/or 2,2-di(hydroxyalkyl)-1,3-propanediol and/or at least one dimer, trimer or polymer of a said di, tri or polyalcohol and/or a reaction product between at least one alkylene oxide, such as ethylene oxide, propylene oxide, 1,3-butylene oxide, 2,4-butylene oxide, cyclohexene oxide, butadiene monoxide and/or phenylethylene oxide, and at least one 1, ⁇ -diol, 2-alkyl-1,3-propanediol, 2,2-dialkyl-1,3-propanediol, 2-alkyl-2-hydroxyalky
  • the preferred di, tri and polyalcohols can suitably be exemplified by 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,6-cyclohexanedimethanol, 5,5-dihydroxymethyl-1,3-dioxane, 2-methyl-1,3-propanediol, 2-methyl-2-ethyl-1,3-propanediol, 2-ethyl-2--butyl-1,3-propanediol, neopentyl glycol, dimethylolpropane, 1,1-dimethylolcyclohexane, glycerol, trimethylolethane, trimethylolpropane, diglycerol, ditrimethylolethane, ditrimethylolpropane, pentaerythritol, dipentaerythritol, anhydroenneaheptitol, sorbito
  • Example 1 refer to preparation of a prepolymer inside the scope of the present invention, which prepolymer is used in Examples 2-4 for preparation of embodiments of the present elastomer.
  • Example 5 refer to preparation of a prepolymer outside the scope of the present invention, which prepolymer is used in Examples 6 and 7 for preparation of reference elastomers. The elastomers obtained in Examples 2-4, 6 and 7 are evaluated in Examples 8-10.
  • Example 11 refers to preparation of a prepolymer inside the scope of the present invention and Examples 12-15 refer to preparation of reference prepolymers outside the scope of the present invention. The prepolymers of Examples 11-15 are used in Example 16 for preparation of embodiment and reference elastomers, which elastomers are evaluated in Examples 17, 18 and 19. The result of evaluations of embodiment and reference elastomers are given in Tables 1-6.
  • a colourless waxy substance having the following characteristics was obtained: Glass transition temperature (Tg), °C 0 Molecular weight (Mn) 1603 Isocyanate content, % 5.33
  • Example 2 30 g of the prepolymer obtained in Example 1 was heated to 120°C and degassed to remove all air. A stoichiometric amount of 1,4-butandiol was now added to the prepolymer for reaction with available free isocyanate groups. Obtained polyurethane elastomer was subsequently cured at 122°C for 24 hours.
  • Example 2 30 g of the prepolymer obtained in Example 1 was heated to 120°C and degassed to remove all air. A stoichiometric amount of a mixture of 1,4-butandiol and trimethylolpropane (1:1 by weight) was now added to the prepolymer for reaction with available free isocyanate groups. Obtained polyurethane elastomer was subsequently cured at 122°C for 24 hours.
  • Example 2 30 g of the prepolymer obtained in Example 1 was heated to 120°C and degassed to remove all air. A stoichiometric amount of an polyethoxylated trimethylolpropane, having an average of 3 ethylene oxide units per molecule (Polyol 3610TM, Perstorp Specialty Chemicals AB, Sweden), was now added to the prepolymer for reaction with available free isocyanate groups. Obtained polyurethane elastomer was subsequently cured at 122°C for 24 hours.
  • Polyol 3610TM Polyethoxylated trimethylolpropane
  • Example 1 was repeated with the difference that ethylene glycol adipate, having a molecular weight of 1000, was used instead of said 2-butyl-2-ethyl-1,3-propanediol polycarbonate diol.
  • Tg glass transition temperature
  • a colourless waxy substance having the following characteristics was obtained: Glass transition temperature (Tg), °C -22 Molecular weight (Mn) 2200 Isocyanate content, % 5.0
  • Example 11 was repeated with the difference that 1,6-hexanediol polycarbonate (DesmophenTM XP 2586, Bayer MaterialScience, Germany) was used instead of said 2-butyl-2-ethyl-1,3-propanediol polycarbonate diol.
  • 1,6-hexanediol polycarbonate (DesmophenTM XP 2586, Bayer MaterialScience, Germany) was used instead of said 2-butyl-2-ethyl-1,3-propanediol polycarbonate diol.
  • Example 11 was repeated with the difference that an adipic acid-ethylene glycol copolymer (FomrezTM 22-112, Crompton Uniroyal Chemical, Great Britain) was used instead of said 2-butyl-2-ethyl-1,3-propanediol polycarbonate diol.
  • an adipic acid-ethylene glycol copolymer (FomrezTM 22-112, Crompton Uniroyal Chemical, Great Britain) was used instead of said 2-butyl-2-ethyl-1,3-propanediol polycarbonate diol.
  • Example 11 was repeated with the difference that a poly(tetramethylene ether) glycol (TerathaneTM 1000, Invista, USA) was used instead of said 2-butyl-2-ethyl-1,3-propanediol polycarbonate diol.
  • a poly(tetramethylene ether) glycol TethaneTM 1000, Invista, USA
  • Example 11 was repeated with the difference that a linear polyester caprolactone (CapaTM 2101A, Solvay, Belgium) was used instead of said 2-butyl-2-ethyl-1,3-propanediol polycarbonate diol.
  • a linear polyester caprolactone CapaTM 2101A, Solvay, Belgium
  • Example 11 180 g of the prepolymer obtained in Example 11 was heated to 90°C and degassed to remove all air. A stoichiometric amount of an 1,4-butanediol was now added to the prepolymer for reaction with available free isocyanate groups. The reaction mixture was degassed a second time before poured into a mould. Obtained polyurethane elastomer was subsequently cured at 120°C for 24 hours. The moulded product was thereafter removed from the mould and post cured for one week at 23°C and 50 % relative humidity.
  • Obtained polyurethane elastomers had following measurement: 245x160x4 mm.
  • Example 16 Three different samples, from each elastomer obtained in Example 16, were cut out (Cutting Die Type ISO 37-2) for tensile testing. The hardness of the samples was measured with a Shore A Durometer and the result is given in Table 4 below.
  • Example 16 Three samples, from each elastomer obtained in Example 16, were cut out (Cutting Die Type ISO 37-2) for hydrolysis resistance testing. The specimens were aged for 14 days at 70°C and 95 % relative humidity in a climate chamber. The hardness of the samples was measured with a Shore A Durometer after the testing and compared to the original values as given in Table 4.
  • Example 16 Three samples, from each elastomer obtained in Example 16, were cut out (Cutting Die Type ISO 37-2) for weather resistance testing.
  • the weather resistance was simulated with accelerated QUV testing according to the following scheme: QUV-A: 4h UV at 60°C, 4h condensation at 50°C, total run time 1000 hours.
  • QUV-A 4h UV at 60°C
  • 4h condensation at 50°C
  • total run time 1000 hours.
  • the retained mechanical properties were determined with a shore A Durometer and tensile testing machine and compared to the original values as given in Table 4.
  • Example 5 Reference) 46 ⁇ 6 Elastomer acc. to Example 6 (Reference) 61 ⁇ 1 Elastomer acc. to Example 7 (Reference) 62 ⁇ 5 Table 3 Sample Tg, °C Elastomer acc. to Example 2 14 Elastomer acc. to Example 3 16 Elastomer acc. to Example 4 15 Elastomer acc. to Example 5 (Reference) -20 Elastomer acc. to Example 6 (Reference) -18 Elastomer acc.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)

Claims (13)

  1. Élastomère polyuréthane obtenu par réaction d'un di, tri ou polyisocyanate, d'un polycarbonate diol et d'un di, tri ou polyalcool caractérisé en ce que ledit polycarbonate diol a un poids moléculaire de 500 à 5 000 g/mole et est obtenu à partir de 2-butyl-2-éthyl-1,3-propanediol ou d'une espèce alcoxylée de celui-ci et d'une source de dioxyde de carbone.
  2. Élastomère polyuréthane selon la revendication 1 caractérisé en ce que ledit polycarbonate diol comprend en outre des unités provenant d'au moins un 2-alkyl-1,3-propanediol ou un 2,2-dialkyl-1,3-propanediol ou une espèce alcoxylée de ceux-ci additionnel(le).
  3. Élastomère polyuréthane selon la revendication 2 caractérisé en ce que ledit au moins un 2-alkyl-1,3-propanediol, 2,2-dialkyl-1,3-propanediol additionnel est le 2-méthyl-1,3-propanediol, le 2-méthyl-2-éthyl-1,3-propanediol ou le 2,2-diméthyl-1,3-propanediol.
  4. Élastomère polyuréthane selon l'une quelconque des revendications 1 à 3 caractérisé en ce que ladite espèce alcoxylée est une espèce éthoxylée, propoxylée ou butoxylée ayant 1 à 20 unités alcoxy.
  5. Élastomère polyuréthane selon l'une quelconque des revendications 1 à 4 caractérisé en ce que ladite source de dioxyde de carbone est le carbonate de diméthyle, le carbonate de diéthyle ou l'urée.
  6. Élastomère polyuréthane selon l'une quelconque des revendications 1 à 5 caractérisé en ce que ledit polycarbonate diol a un poids moléculaire de 500 à 2 500 g/mole.
  7. Élastomère polyuréthane selon l'une quelconque des revendications 1 à 6 caractérisé en ce que ledit di, tri ou polyisocyanate est un di, tri ou polyisocyanate aliphatique, cycloaliphatique ou aromatique.
  8. Élastomère polyuréthane selon l'une quelconque des revendications 1 à 7 caractérisé en ce que ledit di, tri ou polyisocyanate est le diisocyanate d'hexaméthylène, le diisocyanate de 2,4-toluène, le diisocyanate de 2,6-toluène, le diisocyanate de tétraméthylxylylène, le diisocyanate de 1,6-hexane, le diisocyanate de triméthylhexane, le diisocyanate de 1,12-dodécane, le diisocyanate de cyclohexane, le diisocyanate de diphénylméthane, le diisocyanate d'isophorone ou le triisocyanate de nonane.
  9. Élastomère polyuréthane selon l'une quelconque des revendications 1 à 8 caractérisé en ce que ledit di, tri ou polyalcool est au moins un 1,ω-diol, 2-alkyl-1,3-propanediol, 2,2-dialkyl-1,3-propanediol, 2-alkyl-2-hydroxyalkyl-1,3-propanediol ou 2,2-dihydroxyalkyl-1,3-propanediol ou bien est au moins un dimère, trimère ou polymère d'un dit di, tri ou polyalcool.
  10. Élastomère polyuréthane selon l'une quelconque des revendications 1 à 8 caractérisé en ce que ledit di, tri ou polyalcool est le 1,4-butanediol, le 1,5-pentanediol, le 1,6-hexanediol, le 1,6-cyclohexanediméthanol, le 5,5-dihydroxyméthyl-1,3-dioxane, le 2-méthyl-1,3-propanediol, le 2-méthyl-2-éthyl-1,3-propanediol, le 2-éthyl-2-butyl-1,3-propanediol, le néopentyle glycol, le diméthylolpropane, le 1,1-diméthylolcyclohexane, le glycérol, le triméthyloléthane, le triméthylolpropane, le diglycérol, le ditriméthyloléthane, le ditriméthylolpropane, le pentaérythritol, le dipentaérythritol, l'anhydroennéaheptitol, le sorbitol ou le mannitol.
  11. Élastomère polyuréthane selon l'une quelconque des revendications 1 à 8 caractérisé en ce que ledit di, tri ou polyalcool est un produit de réaction entre au moins un oxyde d'alkylène et au moins un 1,ω-diol, 2-alkyl-1,3-propanediol, 2,2-dialkyl-1,3-propanediol, 2-alkyl-2-hydroxyalkyl-1,3-propanediol, 2,2-dihydroxyalkyl-1,3-propanediol ou un dimère, trimère ou polymère d'un dit di, tri ou polyalcool.
  12. Élastomère polyuréthane selon la revendication 11, caractérisé en ce que ledit oxyde d'alkylène est un oxyde d'éthylène, un oxyde de propylène, un oxyde de 1,3-butylène, un oxyde de 2,4-butylène, un oxyde de cyclohexène, un monoxyde de butadiène ou un oxyde de phényléthylène.
  13. Élastomère polyuréthane selon la revendication 11 ou 12, caractérisé en ce que ledit di, tri ou polyalcool est un glycérol, un triméthyloléthane, un triméthylolpropane, un diglycérol, un ditriméthyloléthane, un ditriméthylolpropane, un pentaérythritol, un dipentaérythritol, un anhydroennéaheptitol, un sorbitol ou un mannitol éthoxylé ou propoxylé.
EP06799745A 2005-10-14 2006-10-10 Élastomère polyuréthane Active EP1934272B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE0502284A SE528590C2 (sv) 2005-10-14 2005-10-14 Polyurethane elastomer
PCT/SE2006/001145 WO2007043945A1 (fr) 2005-10-14 2006-10-10 Élastomère polyuréthane

Publications (3)

Publication Number Publication Date
EP1934272A1 EP1934272A1 (fr) 2008-06-25
EP1934272A4 EP1934272A4 (fr) 2011-08-31
EP1934272B1 true EP1934272B1 (fr) 2012-11-28

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US (1) US20090048419A1 (fr)
EP (1) EP1934272B1 (fr)
JP (1) JP2009511706A (fr)
KR (1) KR20080057276A (fr)
CN (1) CN101287773A (fr)
CA (1) CA2624759A1 (fr)
SE (1) SE528590C2 (fr)
WO (1) WO2007043945A1 (fr)

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SE0502284L (sv) 2006-12-27
CN101287773A (zh) 2008-10-15
US20090048419A1 (en) 2009-02-19
EP1934272A4 (fr) 2011-08-31
CA2624759A1 (fr) 2007-04-19
SE528590C2 (sv) 2006-12-27
JP2009511706A (ja) 2009-03-19
WO2007043945A1 (fr) 2007-04-19
EP1934272A1 (fr) 2008-06-25

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